EP0404758A4 - Sulfonamides herbicides. - Google Patents

Sulfonamides herbicides.

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Publication number
EP0404758A4
EP0404758A4 EP19870903635 EP87903635A EP0404758A4 EP 0404758 A4 EP0404758 A4 EP 0404758A4 EP 19870903635 EP19870903635 EP 19870903635 EP 87903635 A EP87903635 A EP 87903635A EP 0404758 A4 EP0404758 A4 EP 0404758A4
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EP
European Patent Office
Prior art keywords
och
compound
growth
controlling
effective amount
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP19870903635
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German (de)
English (en)
Other versions
EP0404758A1 (fr
Inventor
David L Douglass
Marcus P Moon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of EP0404758A4 publication Critical patent/EP0404758A4/fr
Publication of EP0404758A1 publication Critical patent/EP0404758A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof

Definitions

  • This invention relates to novel sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
  • New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
  • the "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge. -SO 2 NHCONH-. linking two aromatic or heteroaromatic rings.
  • U.S. 4.514.211 discloses herbicidal sulfonamides of formula
  • R 6 is H, Cl. Br or C 1 -C 4 alkyl
  • R 6 is H. CH 3 . Cl or Br; and Q 1 is O. S or SO 2 .
  • EP-A-107.979 discloses herbicidal sulfonamides of formula
  • J is. in part.
  • J 18 J 19 n is 0. 1 or 2: R is H or CH 3 ; R 2 is H or C 1 -C 4 alkyl; and R 5 is H or CH 3 .
  • U.S. 4,391, 627 discloses herbicidal sulfonamides of formula
  • W is O or S:
  • R 1 is H. Cl. Br. NO 2 , C 1 -C 3 alkyl. C 1 -C 3 alkoxy. CO 2 R 2 . C(O)NR 3 R 4 . SO 2 R or SO 2 NR 6 R 7 .
  • EP-A-70,698 discloses herbicidal sulfonamides of formula
  • R is H. C 1 -C 4 alkyl. (CH 2 ) m CO 2 R 9 . CH 2 OC 2 H 5 ,
  • R 1 is H, C 1 -C 4 alkyl. CO 2 R 6 . C(O)NR 7 R 8 . C(O)R 10 ,
  • EP-A-168.246 discloses herbicidal sulfonamides of formula
  • R is H or C 1 -C 4 alkyl optionally substituted with 0-3 halogen atoms selected from 1-3 F. 1-2 Cl or 1 Br. C 1 -C 4 alkylthio. C 1 -C 4 alkoxy. CH 2 OCH 3 , CH 2 CH 2 OCH 3 or CH 2 SCH 3 ;
  • R 2 is H or CH 3 ;
  • W is O, S or NR 3 .
  • U.S. 4,502.882 discloses, in part, herbicidal sulfonamides of formula
  • W is O, S, SO or SO 2 ;
  • W 1 is O. S, SO or SO 2 ;
  • R 1 is H or CH 3 : and
  • R 2 is H or C 1 -C 4 alkyl.
  • U.S. 4,578.108 discloses, in part, herbicidal sulfonamides of formula
  • Q is O, S(O) n or NR 3 : n is O, 1 or 2; R 1 is H, CH 3 . Cl or F; R 6 is H, Cl or F: R 7 is H, Cl or F: and R 8 is H, Cl or F.
  • A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a nonaromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the -SO- or SO 2 - group, and R 2 is hydrogen, halogen, nitro.
  • C1-C 4 alkylthio C 1 -C 4 alkylsulfinyl. C 1 - C 4 - alkylsulfonyl or C 2 -C 5 alkoxyalkoxy; and R 1 is H. halogen. NO 2 , C 1 -C 4 alkyl. C 1 -C 4 haloalkyl. C 1 -C 4 alkoxy. C 1 -C 4 haloalkoxy. C 1 -C 4 alkoxycarbonyl. C 1 -C 4 alkylthio. C 1 -C 4 alkylsulfinyl. C 1 -C 4 alkylsulfonyl or C 2 -C 5 alkoxyalkoxy.
  • South African Patent Application 84/3522 (Swiss priority 5/11/83, published 11/11/84) discloses herbicidal sulfonamides of formula
  • R 1 is H. halogen. NO 2 . C 1 -C 4 alkyl. C 1 -C 4 haloalkyl. CN. XR 5 , COXR 6 , CONR 7 R 8 . SOR 9 or SO 2 R 10 : and
  • A is an unsubstituted or substituted unsaturated bridge of 4 atoms, of the formula
  • R 20 and R 30 are H or halogen and R 10 is carbamoyl N-substituted by a C 1 -C 4 aliphatic or C 3 -C 4 cycloaliphatic group.
  • This invention relates to novel compounds of Formula I, agriculturally suitable compositions containing them, and their method-of-use as general preemergence and/or postemergence herbicides or plant growth regulants.
  • W is O or S
  • R is H or CH 3 ;
  • E is a single bond.
  • R 1 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl. halogen, nitro, C 1 -C 3 alkoxy.
  • SO 2 NR a R b C 1 -C 3 alkylthio, C 1 -C 3 alkylsulfinyl, C 1 -C 3 alkylsulfonyl.
  • CO 2 R c C 1 -C 3 haloalkoxy.
  • CH 2 N 3 or NR d R e
  • R a is H, C 1 -C 4 alkyl. C 2 -C 3 cyanoalkyl. methoxy or ethoxy;
  • R b is H. C 1 -C 4 alkyl or C 3 -C 4 alkenyl: or
  • R a and R b may be taken together as -(CH 2 ) 3 -, -(CH 2 ) 4 -, -(CH 2 ) 5 - or -CH 2 CH 2 OCH 2 CH 2 -;
  • R C is C 1 -C 4 . alkyl. C 3 -C 4 alkenyl. C 3 -C 4 alkynyl.
  • C 2 -C 4 haloalkyl C 2 -C 3 cyanoalkyl. C 5 -C 6 cycloalkyl. C 4 -C 7 cycloalkylalkyl or C 2 -C 4 alkoxyalkyl;
  • R d and R e are independently H or C 1 -C 2 alkyl
  • Q 1 is S, SO 2 or NR 2 :
  • Q 2 is O, S or NR 2 :
  • Q 3 is O, S or NR 3 ;
  • Q 4 . is O. S or NR4; n is O. 1 or 2;
  • R 3 is H or C 1 -C 3 alkyl:
  • R 4 is H or CH 3 :
  • R 5 is H, halogen. CH 3, CH 2 CH 3 , OCH 3 , OCH 2 CH 3 , OCF 2 H or halomethyl;
  • R 6 is C 1 -C 4 alkyl ;
  • X is H, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 haloalkyl.
  • halogen. C 2 -C 5 alkoxyalkyl, C 2 -C 5 alkoxyalkoxy. amino.
  • Y is H. C 1 -C 4 alkyl. C 1 -C 4 alkoxy.
  • L 1 and L 2 are independently O or S;
  • R f is H or C 1 -C 3 alkyl
  • R g and R h are independently C 1 -C 3 alkyl:
  • Z is CH or N
  • Z 1 is CH or N
  • Y 1 is O or CH 2 :
  • X 1 is CH 3 , OCH 3 , OC 2 H 5 or OCF 2 H;
  • X 2 is CH3, C 2 H 5 or CH2CF 3 :
  • Y 2 is OCH 3 , OC 2 H 5 , SCH 3 , SC 2 H 5 . CH 3 or CH 2 CH 3 :
  • X 3 is CH 3 or OCH 3 ;
  • Y 3 is H or CH 3 ;
  • X 4 is CH 3 , OCH 3 , OC 2 H 5 . CH 2 OCH 3 or Cl;
  • Y 4 is CH 3 , OCH 3 , OC 2, H 5 or cl; and their agriculturally suitable salts; provided that a) when X is Cl, F, Br or I, then Z is CH and Y is OCH 3 . OC 2 H 5 , N(OCH 3 )CH 3 , NHCH 3 , N(CH 3 ) 2 or OCF 2 H; b) when X or Y is C 1 haloalkoxy. then Z is CH; c) X 4 and Y 4 are not simultaneously Cl; d) when W is S, then E is a single bond.
  • R is H, A is A-1 and Y is CH 3 . OCH 3 , OC 2 H 5 , CH 2 OCH 3 .
  • alkyl used either alone or in compound words such as "alkylthio" or "haloalkyl”. denotes straight chain or branched alkyl, e.g. methyl, ethyl, n-propyl. isopropyl or the different butyl isomers.
  • Alkoxy denotes methoxy, ethoxy. n-propyloxy. isopropyloxy and the different butyl isomers.
  • Alkynyl denotes straight chain or branch alkynes, e.g. ethynyl. 1-propynyl, 2-propynyl and the different butynyl isomers.
  • Alkylsulfonyl denotes methylsulfonyl, ethylsulfonyl and the different propylsulfonyl isomers.
  • Alkylthio. alkylsulfinyl. alkylamino. alkylsulfamoyl, etc. are defined in an analogous manner.
  • Cycloalkyl denotes, e.g.. cyclopropyl. cyclobutyl and cyclopentyl.
  • halogen either alone or in compound words such as “haloalkyl”. denotes fluorine, chlorine, bromine and iodine.
  • C i -C j The total number of carbon atoms in a substituent group as indicated by the C i -C j prefix where i and j are numbers from 1 to 5.
  • C 1 -C 3 alkylsulfonyl would designate methylsulfonyl through propylsulfonyl.
  • C 2 alkoxyalkoxy would designate OCH 2 OCH 3 .
  • Compounds preferred for reasons of increased ease of synthesis and/or greater herbicidal efficacy are:
  • X is C 1 -C 2 alkyl, C 1 -C 2 alkoxy, Cl, F, Br. I. OCF 2 H, CH 2 F, CF 3 , OCH 2 CH 2 F, OCH 2 CHF 2 , OCH 2 CF 3 , CH 2 C 1 or CH 2 Br; and Y is H, C 1 -C 2 alkyl. C 1 -C 2 alkoxy.
  • R is H
  • R 1 is H. Cl, CH 3 or OCH 3 ;
  • X is CH 3 , OCH 3 , Cl, OC 2 H 5 or OCF 2 H;
  • Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 , NHCH 3 . CH(OCH 3 ) 2 or cyclopropyl.
  • A is A-1;
  • X is CH 3 , OCH 3 , OCH 2 CH 3 , Cl or OCF 2 H;
  • Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 , NHCH 3 , CH(OCH 3 ) 2 or cyclopropyl. 15. Compounds of Preferred 3 where
  • R is H
  • R 1 is H:
  • R 2 is H or CH 3 ;
  • A is A-1;
  • X is CH 3 , OCH 3 , OCH 2 CH 3 , Cl or OCF 2 H;
  • Y is CH 3 , OCH 3 , C 2 H 5 , CH 2 OCH 3 .
  • the compounds of this invention are highly active as preemergent and/or postemergent herbicides or plant growth regulants. Some of the compounds have utility for selective weed control in crops such as oilseed rape, rice, barley, cotton and sugar beets.
  • the compounds of Formula I can be prepared by one or more of the methods described below in Equations 1 through 5.
  • R, A and W are as previously defined. Equation 1
  • reaction is carried out at 25o to 100oC in an inert, aprotic solvent such as methylene chloride or xylene for 0.5 to 24 hours as taught in U.S. Patent 4.127.405.
  • aprotic solvent such as methylene chloride or xylene
  • the reaction is carried out at 50o to 100oC in a solvent such as dioxane for 0.5 to 24 hours.
  • the required carbamates VI are prepared by reacting the corresponding sulfonamides IV with diphenylcarbonate in the presence of a strong base.
  • the reaction is carried out at 0° to 50°C in a solvent such as acetonitrile or dioxane in the presence of a non-nucleophilic base such as DBU for 0.2 to 24 hours.
  • a solvent such as acetonitrile or dioxane
  • a non-nucleophilic base such as DBU for 0.2 to 24 hours.
  • the required phenylcarbamate VII are prepared by reacting the corresponding heterocyclic amines III with diphenylcarbonate or phenylchloroformate in the presence of a strong base.
  • the reaction is carried out at 25° to 40°C in a solvent such as methylene chloride for 10 to 96 hours under an inert atmosphere.
  • the required carbamates VIII are prepared by reacting the corresponding amines III with dimethylcarbonate or methyl chloroformate in the presence of a strong base.
  • many of the sulfonyl isocyanates of Formula Ila can be prepared by the reaction of sulfonamides of Formula IV with phosgene, in the presence of n-butylisocyanate and a tertiary amine catalyst, at reflux in a solvent such as xylene by the method of U.S. Patent 4.238,621. Equation 6
  • the sulfonyl isocyanates can also be prepared from the sulfonamides by a two step procedure involving (a) reacting the sulfonamides with n-butylisocyanate in the presence of a base such as K 2 CO 3 at reflux in an inert solvent such as 2-butanone forming a n-butylsulfonylurea; and (b) reacting this compound with phosgene and a tertiary amine catalyst at reflux in xylene solvent.
  • the method is similar to a procedure taught by Ulrich and Sayigh, Newer Methods of Preparative Organic Chemistry. Vol. VI, p. 223-241, Academic Press, New York and London. W. Foerst Ed.
  • Equation 7 An alternative two step procedure for preparing sulfonyl isocyanates of Formula Ila is shown in Equation 7. Equation 7
  • the sulfonamides of Formula IV are heated with excess thionyl chloride forming N-sulfinyl sulfonamides of Formula IX.
  • the intermediate N-sulfinyl sulfonamides are heated in an inert solvent such as toluene with phosgene (e.g. 2-3 equivalents) and pyridine (e.g. 0.1 equivalents) to give sulfonyl isocyanates of Formula Ila.
  • the method is similar to that taught by Ulrich et al. J. Org. Chem 34. 3200 (1969).
  • Equation 8 many of the sulfonyl isocyanates of Formula Ila can be prepared by reacting the corresponding sulfonyl chlorides X with cyanic acid salts. Equation 8
  • the reaction is carried out at 25° to 100oC in an inert aprotic solvent such as acetonitrile for 0.5-24 hours in the presence of phosphorus pentoxide and an alkali metal salt such as lithium iodide.
  • an inert aprotic solvent such as acetonitrile
  • an alkali metal salt such as lithium iodide.
  • Equation 9 Many of the sulfonyl isocyanates of Formula llb can be prepared, as shown in Equation 9. by contacting phenols of Formula XI with chlorosulfonyl isocyanate according to the teachings of Lohaus, Chem. Ber.. 105. 2791 (1972) or U.S. Patent 4.191.553. Equation 9
  • sulfonyl isothiocyanates of Formula lie can be prepared, as shown in Equation 10, by contacting the sulfonamides of Formula IV with carbon disulfide in the presence of two equivalents of a strong base. The resulting salt is then reacted with phosgene according to the teachings of K. Hartke, Arch. Pharm.. 299. 174 (1966).
  • the sulfonamides of Formula IV of Equations 2, 4, 5, 6, 7 and 10 as well as the other sulfonamides required to prepare the compounds of this invention can be prepared from the corresponding sulfonyl chlorides of Formula X by contacting with either anhydrous or aqueous ammonia as shown in Equation 11. Equation 11
  • Equation 12 many sulfonamides of Formula IV can be prepared from the corresponding lithium reagent of Formula XII as shown in Equation 12.
  • M represents the lithium moiety of the metalated reagents. Equation 12
  • the metalated intermediates XII are contacted with sulfur dioxide to afford the lithium sulfinates of Formula XIII.
  • Intermediates XIII are subsequently contacted with hydroxylamine-O-sulfonic acid to afford the sulfonamides of Formula IV.
  • the procedure for preparing similar sulfonamides by this method is taught in South African Patent Appln. 85-1568.
  • sulfonamides IV can be prepared by dealkylation of their corresponding N-t-butyl sulfonamides XIV as shown in Equation 13. Equation 13
  • the reaction is carried out by contacting the N-t-but ⁇ l sulfonamide XIV with a strong acid such as trifluoroacetic acid or methanolic HCl at 25° to 50°C for 0.5 to 24 hours.
  • a strong acid such as trifluoroacetic acid or methanolic HCl
  • the N-t-butyl sulfonamides XIV are readily prepared by reacting sulfonyl chlorides X with t-butylamine and are useful either as an aid in purification, or to enhance solubility for subsequent reactions, or to protect the sulfonamide function from competing with reactions at other parts of the molecule.
  • the sulfonyl chlorides of Formula X of Equations 8 and 11 are important intermediates for the preparation of the compounds of this invention.
  • the synthesis of the required sulfonyl chloride intermediates are described in Equations 14 through 20.
  • many of the sulfonyl chlorides of Formula X can be prepared by chlorosulfonating the parent ring compounds of Formula XV. Equation 14
  • Equation 15 many of the sulfonyl chlorides of Formula X can be prepared from the corresponding amines XVI by a Meerwein reaction. Equation 15
  • reaction involves diazotization of the amine XVI with sodium nitrite in aqueous HCl, followed by reaction of the diazonium salt with sulfur dioxide and cupric chloride in acetic acid analogous to the teachings of Yale and Sowinski. J.. Orq . Chem. . 25. 1824 ( 1960) .
  • Equation 16 j / 2 J-SO 2 Cl
  • the amine hydrochloride salts XVIa are diazotized with an alkylnitrite in an organic solvent, such as acetonitrile or acetone, and the resulting diazonium salts are reacted with sulfur dioxide and cupric chloride to give sulfonyl chlorides X.
  • an organic solvent such as acetonitrile or acetone
  • sulfonyl chlorides of Formula X can also be prepared by oxidative chlorination of the corresponding thio compounds of Formula XVII as shown in Equation 17.
  • R' is H, alkyl. benzyl or carbamoyl. Equation 17
  • reaction is carried out by addition of molecular chlorine or a chlorine equivalent to the thio compound in the presence of water at 0° to 80oC in an aliphatic carboxylic acid solvent such as acetic acid or an inert organic solvent such as dichioroethane for 1 to 24 hours.
  • an aliphatic carboxylic acid solvent such as acetic acid or an inert organic solvent such as dichioroethane for 1 to 24 hours.
  • the thiol XVIIa is contacted with excess hydrogen peroxide in the presence of base to give a sulfonic acid salt which in turn is converted to the desired sulfonyl chloride by contacting with a suitable reagent such as thionyl chloride or phosphorous pentachloride as known to one skilled in the art.
  • a suitable reagent such as thionyl chloride or phosphorous pentachloride as known to one skilled in the art.
  • Thiols XVIIa can also be oxidized to sulfonyl chlorides X with sodium hypochlorite using the methods taught in South African Patent Appln. 84/8844.
  • sulfonyl chlorides of Formula X can be prepared from the corresponding lithium or Grignard reagent of Formula XII and sulfuryl chloride as shown in Equation 19.
  • M represents either the lithium or MgX' moiety of the metalated reagent. Equation 19
  • the phenol XI is first reacted with N,N-di- methylthiocarbamoyl chloride in the presence of a base.
  • the resulting O-aryl-N.N-dimethylthiocarbamate XIX is then heated at 150°C to 300°C for 2 to 24 hours as taught by Newman and Karnes J. Orq. Chem.. 31. 3980
  • the reaction is carried out in a solvent such as DMF at 25° to 150oC for 0.5 to 24 hours.
  • a solvent such as DMF at 25° to 150oC for 0.5 to 24 hours.
  • the halocompounds XX must not contain functionality which can be attacked by a mercaptide anion as will be known to one skilled in the art.
  • Equation 15 The amines of Formula XVI in Equation 15 can be prepared by reduction of the corresponding nitro compounds of Formula XXI as shown in Equation 23. Equation 23
  • amines of Formula XVI are versatile intermediates for preparing phenols of Formula XI and halocompounds of Formula XX by the diazotization reactions of Equation 24.
  • Compounds XXII represent diazonium salts derived from amines XVI. Equation 24
  • Phenols of Formula XI can also be prepared from ethers of Formula XXIII.
  • A represents a suitable alkyl or arylalkyl protecting group, as shown in Equation 25.
  • T. Green teaches methods for deprotecting ethers to phenols in "Protective Groups in Organic Synthesis.” Ch. 2, p. 10. Wiley, 1981. Equation 25
  • Metalated intermediates of Formula XII in Equations 12 and 19 can be prepared from halocompounds of
  • Equation 23 can be prepared from ring compounds XV by the reaction shown in Equation 26.
  • J J-1 (XXIVa, XXIVb. XXIVc) can be prepared by the diazotization reactions of Equation 27. Methods for these reactions are described by a) L. L. Bambas. "The
  • heterocyclic amines of Formula III in Equations 1 and 3 can be prepared by methods known in the literature, or simple modifications thereof, by one skilled in the art.
  • Example 9 1-Methyl-1H-benzotriazole-4-sulfonylisocyanate To a stirred mixture of N-[(butylaraino)carbonyl]-1-methyl-1H-benzotriazole-4- sulfonamide (8.25g), 1.4-diazabicyclo[2.2,2]octane (catalytic amount), and xylenes (175mL). heated at reflux under a nitrogen atmosphere, was added phosgene (2mL) in small portions over 1 hour. The resulting suspension was heated an additional 0.5 hours and was cooled prior to filtering off the insoluble material.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions. emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inert diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Active ingredient plus at least one of a Surfactant or a Diluent equals 100 weight percent.
  • Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.
  • Typical solid diluents are described in Watkins. et al., "Handbook of Insecticide Dust Diluents and Carriers”. 2nd Ed., Dorland Books, Caldwell, New Jersey, but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts.
  • Typical liquid diluents and solvents are described in Marsden, “Solvents Guide,” 2nd Ed., Interscience, New York. 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
  • compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example. Littler, U.S. Patent 3,060.084). Granules and pellets may be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See J. E. Browning. "Agglomeration”. Chemical Engineering. December 4. 1967, pp. 147ff. and "Perry's Chemical
  • the ingredients are blended, coarsely hammermilled and then air-milled to produce particles essentially all below 10 microns in diameter.
  • the product is reblended before packaging.
  • Example 14 Granule Wettable Powder of Example 13 5% attapulgite granules 95%
  • a slurry of wettable powder containing 25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.
  • the ingredients are blended, hammer-milled and then moistened with about 12% water.
  • the mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings).
  • the granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.
  • the ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.
  • N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1,2.3-benzothiadiazole-4-sulfonamide 40% polyacrylic acid thickener 0.3% dodecylphenol polyethylene glycol ether 0.5% disodium phosphate 1% monosodium phosphate 0.5% polyvinyl alcohol 1.0% water 56.7% The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.
  • the salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.
  • the active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.
  • Example 23 The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat. until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.
  • Example 23 Example 23
  • Example 24 The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
  • Example 24 The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.
  • the ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns.
  • the material is sifted through a U.S.S. No. 50 screen and then packaged.
  • the ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size.
  • the material is reblended and then packaged.
  • the active ingredient is blended with attapulgite and then passed through a hammer-mill to produce particles substantially all below 200 microns.
  • the ground concentrate is then blended with powdered pyrophyllite until homogeneous.
  • Example 28 Emulsifiable Concentrate N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-5- methoxy-1,2,3-benzothiadiazole-4-sulfonamide 10% chlorobenzene 84% sorbitan monostearate and polyoxyethylene condensates thereof 6% The ingredients are combined and stirred to produce a solution which can be emulsified in water for application.
  • the subject compounds are useful to modify plant growth.
  • the rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth regulants or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc.
  • the subject compounds should be applied at levels of around 0.001 to 20 kg/ha, the lower rates being suggested for use on lighter soils and/or those having a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.
  • the compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole. uracil.
  • DESMEDIPHAM BETANEX ®
  • PYRAMIN ® Isopropyl carbanilate PYRAZON
  • G growth retardation
  • H formative effect
  • U unusual pigmentation
  • X axillary stimulation
  • S albinism
  • Three round pans were filled with Sassafras sandy loam soil.
  • One pan was planted with nutsedge (Cyperus rotundus) tubers, crabgrass (Diqitaria sanquinalis). sicklepod (Cassia obtusifolia). jimsonweed (Datura stramonium), velvetleaf (Abutilon theophrasti). lambsquarters (Chenopodium album). rice (Orvza sativa) and teaweed (Sida spinosa).
  • the second pot was planted with green foxtail (Setaria viridis). cocklebur (Xantium pensylvanicum). morningglory (Ipomoea hederacea).
  • Three round pans (25 cm diameter by 12.5 cm deep) were filled with Sassafras sandy loam soil.
  • One pan was planted with nutsedge tubers, crabgrass. sicklepod, jimsonweed, velvetleaf, lambsquarters, rice and teaweed.
  • the second pot was planted with green foxtail, cocklebur, morningglory, cotton, johnsongrass. barnyardgrass. corn, soybean and giant foxtail.
  • the third pot was planted with wheat, barley, wild buckwheat, cheatgrass. sugarbeet. wild oat, viola, blackgrass and rape.
  • the three pans were sprayed preemer- gence with the chemicals dissolved in a non-phytotoxic solvent.
  • Treated plants and controls were maintained in the greenhouse for 24 days, then all rated plants were compared to controls and visually rated for plant response.
  • Two plastic windowsill trays were filled with planting medium.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Nouveaux composés herbicides à base de sulfonilurée, compositions ayant une utilisation appropriée à l'agriculture, et procédé d'utilisation de ces composés et compositions en tant qu'herbicides généraux d'émergence antérieure et/ou postérieure ou leur utilisation en tant qu'agents régulateurs de la croissance des plantes.
EP87903635A 1986-05-23 1987-05-21 Sulfonamides herbicides Withdrawn EP0404758A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US86823986A 1986-05-23 1986-05-23
US868239 1986-05-23
US39492 1987-04-16
US07/039,492 US4746356A (en) 1986-05-23 1987-04-16 Herbicidal sulfonamides

Publications (2)

Publication Number Publication Date
EP0404758A4 true EP0404758A4 (fr) 1989-08-30
EP0404758A1 EP0404758A1 (fr) 1991-01-02

Family

ID=26716176

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EP87903635A Withdrawn EP0404758A1 (fr) 1986-05-23 1987-05-21 Sulfonamides herbicides

Country Status (4)

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US (1) US4746356A (fr)
EP (1) EP0404758A1 (fr)
AU (1) AU606069B2 (fr)
WO (1) WO1987007114A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4921527A (en) * 1987-07-31 1990-05-01 E. I. Du Pont De Nemours And Company Herbicidal sulfonamides
DE59208670D1 (de) * 1991-04-11 1997-08-14 Hoechst Schering Agrevo Gmbh Verfahren zur Herstellung von 2-Pyridylsulfonylharnstoffen und Thiadiazolopyridine als Zwischenprodukte in diesem Verfahren

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD134184A1 (de) * 1977-11-28 1979-02-14 Heinz Dehne Herbizide mittel
EP0082681A2 (fr) * 1981-12-17 1983-06-29 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
EP0168264A2 (fr) * 1984-07-13 1986-01-15 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
EP0125864B1 (fr) * 1983-05-09 1987-04-08 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4634465A (en) * 1982-07-16 1987-01-06 Ciba-Geigy Corporation Fused N-phenylsulfonyl-N'-pyrimidinylureas and N-phenylsulfonyl-N'triazinylureas
US4589911A (en) * 1983-05-11 1986-05-20 Ciba-Geigy Corporation Fused N-phenylsulfonyl-N-triazinylureas
US4546179A (en) * 1983-11-23 1985-10-08 E. I. Du Pont De Nemours And Company Process for preparing sulfonylureas
CA1222746A (fr) * 1984-05-07 1987-06-09 E. I. Du Pont De Nemours And Company Nouveaux derives de substitution phenyliques de sulfonamides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD134184A1 (de) * 1977-11-28 1979-02-14 Heinz Dehne Herbizide mittel
EP0082681A2 (fr) * 1981-12-17 1983-06-29 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
EP0125864B1 (fr) * 1983-05-09 1987-04-08 E.I. Du Pont De Nemours And Company Sulfonamides herbicides
EP0168264A2 (fr) * 1984-07-13 1986-01-15 E.I. Du Pont De Nemours And Company Sulfonamides herbicides

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of WO8707114A1 *

Also Published As

Publication number Publication date
AU606069B2 (en) 1991-01-31
AU7512087A (en) 1987-12-22
WO1987007114A1 (fr) 1987-12-03
US4746356A (en) 1988-05-24
EP0404758A1 (fr) 1991-01-02

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